Where to Stay in Key West, FL: Best Hotels with Pools

Key West, FL, is a vibrant tapestry of sun-soaked beaches, rich history, and lively nightlife that beckons travelers from all corners of the globe. With its laid-back atmosphere, colorful architecture, and mouthwatering seafood, this tropical paradise offers an unforgettable escape filled with unique cultural experiences.

When it comes to unwinding after a day of exploration, choosing a hotel with a pool can elevate your stay to new heights of relaxation. The right accommodations not only enhance your vacation experience but also provide a perfect base for discovering all that Key West has to offer. Dive into our comprehensive guide, where you'll find the best places to stay, nearby neighborhoods, top attractions, and helpful travel tips.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Recommended accommodation

Parrot Key Hotel & Villas
Parrot Key Hotel & Villas
Resort
Key West, FL, USA

Accommodations, Pools, Resorts, Parking, Romantic, Boutique, Gites, 4-star, Gostinicies, Rooms, Alberghi, Lodgings, Places to stay, Family, Accessible hotels

The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
Resort
Key West, USA

Luxury, Accommodations, Pools, Resorts, Parking, Romantic, Gites, 4-star, Gostinicies, Rooms, Alberghi, Lodgings, Places to stay, Family, Accessible hotels

Margaritaville Beach House Key West
Margaritaville Beach House Key West
Hotel
Key West, FL, USA

Accommodations, Pools, Parking, Romantic, Gites, Pet-friendly, 3-star, Gostinicies, Rooms, Alberghi, Lodgings, Hot tubs, Places to stay, Family, Accessible hotels

Amsterdam's Curry Mansion Inn
Amsterdam's Curry Mansion Inn
Bed & Breakfast
Key West, USA

Child Friendly, Internet, Wheelchair Accessible, Air Conditioner, Balcony/Terrace, Pet Friendly, Pool, Smoking, Parking, Laundry, Breakfast

Hilton Garden Inn Key West/The Keys Collection
Hilton Garden Inn Key West/The Keys Collection
Hotel
Key West, FL, USA

Accommodations, Pools, Parking, Romantic, Gites, Hilton , 3-star, Gostinicies, Rooms, Alberghi, Lodgings, Hot tubs, Places to stay, Accessible hotels

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Things to do and Activities in Key West

🎫 Local Experiences & Attractions in Key West, USA

✨ Things to Do

Sunset Celebration at Mallory Square: Join locals and travelers for a nightly sunset celebration featuring street performers, local artists, and food vendors at Mallory Square in Key West, USA.

🔗 Check Availability on GetYourGuide

Snorkeling at John Pennekamp Coral Reef State Park: Explore vibrant coral reefs teeming with marine life during a snorkeling trip from Key West, USA. Guided tours provide equipment and safety briefings.

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Key West Food Tour: Experience the diverse culinary scene of Key West, USA, by tasting local specialties on a guided food tour that showcases popular eateries and hidden spots.

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📍 Top Attractions

Ernest Hemingway Home and Museum: Visit the former residence of famous author Ernest Hemingway, where you can see his writing studio and explore lush gardens. Visitor Tip: Arrive early to avoid crowds.

🔗 Book Entry Tickets

Key West Lighthouse and Keeper's Quarters: Climb to the top of this historic lighthouse for panoramic views of Key West, USA, and learn about its maritime history in the adjoining museum.

🔗 Book Entry Tickets

Dry Tortugas National Park: Take a ferry or seaplane to this remote national park, known for its historic Fort Jefferson and pristine beaches. It's ideal for nature lovers and history buffs alike.

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Travel Tips for Key West

💡 Essential Logistics & Insider Tips for Key West, USA

🚆 Getting Around

The Core Tip: Visitors primarily get around Key West by walking or biking due to its compact size and walkable streets.

The Pro Move: Rent a bicycle from local shops to explore the island at your own pace while avoiding parking hassles.

📅 Timing Your Trip

The Core Tip: The peak tourist season runs from December to April, coinciding with pleasant weather and numerous festivals.

The Pro Move: Visit popular attractions like the Ernest Hemingway Home and Museum early in the morning to avoid crowds.

🚶 Getting Around Safely

The Core Tip: Key West is very pedestrian-friendly, with well-marked sidewalks and bike lanes enhancing safety.

The Pro Move: Use crosswalks and remain aware of traffic, especially on busier streets like Duval Street.

💳 Money & Payments

The Core Tip: Most hotels, restaurants, and attractions accept credit cards, making transactions straightforward.

The Pro Move: Keep small cash on hand for local markets or tips, where card payment might not be accepted.

✈️ Airport / Arrival Tips

The Core Tip: From Key West International Airport, visitors can access taxis and rideshare services for convenient transportation.

The Pro Move: Follow airport signage directly to the designated pickup areas to streamline your arrival process.

Where to Stay in Key West, FL: Best Hotels with Pools properties on the Map